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« On the Road with Kevin »
Entry 2


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Leaving the Rockies, Montana that is.
I don’t know about anyone else, but I can certainly think of no better way to start a cross-country trip than to pass an elderly gentleman on the roads of Montana who is holding a cigarette out of the window with his left hand, fiddling with the radio with his right hand, wearing some industrial-sized spectacles, cradling his cell phone awkwardly in his neck, has a blue sticker hanging from the rearview mirror, and is swerving wildly all over the asphalt.

If that doesn’t build confidence in your fellow American driver, I don’t know what will. I have never seen anything like it before, but it made for some very contemplative thoughts as I headed eastward on my first day of the journey towards Minneapolis.


And welcome back to you if you just so happen to be reading the second helping of these journal entries. Unfortunately, we decided to postpone the trip due to unforeseen circumstances, and I only made it to the eastern edge of Montana before I had to turn back around. However, I am more than happy to fill you in on the travails of driving across half of Montana and then back again.


I know, I couldn’t pull that one off for too long while trying to keep a straight face. In all actuality, of course, the trip from coast to coast is well under way and is still moving ahead as planned. I packed up my Ford Explorer and embarked on I-90 East, as my first stop was to visit some great friends in Minneapolis who used to live in Montana. It is about a 14-15 hour drive from Bozeman to Minneapolis, though, so I tried to make it as far as I could that first day after getting a late start.

I ended up resting my head that initial night in Bismarck, North Dakota, and managed to make it to Minneapolis the following day. I made a note to contact the Minnesota state government later, however, for claims of false advertising regarding their slogan of “The Land of 10,000 Lakes.” At least from what I could tell, I would be hard pressed to believe there could be any more than 9,993 lakes in the entire state.


Some of the trip details. In all seriousness, it has been an interesting experience trying to figure out if something like this trip could actually be done, and what would be the best way to go about doing so. One of my biggest concerns was not wanting any of the women I would be meeting to feel any less special simply because I was meeting other people along the way as well.

As I mentioned in the earlier entry, I had just felt I knew some inviting women through the web site, but also that I didn’t really KNOW anybody yet, and I just wanted to set out to learn more. Sure, there were some that I thought I might have a stronger chance to connect with, or vice-versa, but again, I kept coming back to not knowing that until I had met somebody in person.



I guess the most basic way I can put it is possibly this: I just wanted to explore the potential of meeting someone I might really like, and who might like me back. That’s it. I tried to not make the underlying reason for why I was doing this too complicated. Of course I was open to meeting somebody amazing and looking into things down the road, but I was not hoping to become engaged or anything like that as a result of this trip. I just wanted to hang out a bit to see if I could meet a cool person who might feel the same way about me. To me at least, that’s sort of what we all do in our day to day lives anyway in our crazy search for finding someone to share our time with.

I tried with a great deal of care to get advice before leaving from some of my women friends to see if it was even feasible that women would want to meet a guy in such a manner as this trip, or the most sincere ways to go about this or that from a woman’s point of view. I think the overwhelming response I got back was “yes,” because it takes a lot of the pressure off the situation. I also realized, however, that probably a few of the women I had been corresponding with might be a little more apprehensive, which I guess is sort of understandable.


Most responses were positive, but... One woman from California I had emailed back and forth with several times replied solely with a “no thank you” in her message after I had asked her about the potential of catching up with her. Another gal from Pennsylvania who seemed to be pretty witty and charming in her letters stated that our correspondence was more of just an enjoyable thing for her, as she never thought we would actually meet.

When faced with the very conceivable chance of seeing each other now, she said that she wasn’t maybe ready to have someone in her life at the moment, as there was even a big move overseas for school at the beginning of the new year. So there were some women who didn’t want to be a part of the experience (which again, I can acknowledge), but I think the majority of people took it just as I meant it: a fun and different avenue to try out.


Anyway, I stayed a short time with my friends, Josh and Lindsey, in Minneapolis and then proceeded to head to Chicago to meet the first woman, “Annah.” In some respects, I reckon (Montana speak for I guess) this trip was also appealing because I knew I would be able to see many of my friends along the way that I may not be able to see again for quite some time.


Why did the badger cross the road? The drive to Chicago was a highly pleasurable one, as it was my first time being in Wisconsin and the views were simply breathtaking. It was very much how I pictured it to be, with the warm, autumn colors in the deciduous trees and the gently rolling hills. The West definitely has its beauty, but there is something to be said for the softer feeling that seemed to encompass Wisconsin. It reminded me very much of the scenes from everyone’s favorite PBS landscape painter, Bob Ross. Now if only I could get my coiffure to look anything similar to how his did and find a happy tree or two, I figured I’d be set.


I pulled into Annah’s small town, which is about 60 miles west of Chicago, in the early evening and tried to wrap my head around the fact that I was actually doing this; that I was actually meeting the first person that would ultimately take me on a journey from Montana, to the Atlantic, to the Pacific, and back to Montana again. And why hadn’t anybody tried to stop me! It was one of the more surreal moments in my life, as I was just trying to grasp how it had come to this point. I was very excited about meeting her and getting the real part of the trip going, but I also slowly began to comprehend just how big an undertaking this entire experience truly was.


Annah’s town is actually where most of the movie Groundhog Day, with Bill Murray, takes place. And amazingly, her friend runs a hotel called the Town Square Inn that just so happens to sit on the town square where a good portion of that movie was filmed. Her friend had insisted that since it was the middle of the week, and some rooms would be vacant anyway, that I should stay there to absorb all the town had to offer. I couldn’t resist that generous invitation, so Annah and I decided to meet at the hotel. I wasn’t too nervous about meeting her, as I figure the only thing you can really do is follow the old adage to just be yourself. I think you’re probably not human, though, if you don’t have at least a couple butterflies twittering around in your stomach. But I guess it’s up to the other person to take away their own impressions of you, and there’s not much you can do about that if you’re just being true to yourself.


So after I threw up on the sidewalk, I knew it was time to go meet her. Annah opened the door and was definitely taller than I had expected, which is usually a good thing as I’m 6’2.” She was probably around 5’9” and had longer, brunette hair.

And I must admit that she was wearing a getup (or “outfit,” if I can use that word) that has always been very attractive to me for some reason: a nice skirt, some cool stockings, and a sharp shirt of some kind.

Or maybe it was a blouse. Or a sweater. Or perhaps it was a top. I have felt for years that the terms and sizes used in women’s clothing serve no greater purpose than to confuse the male mind. I actually DO know what most things mean, but the variances are still mind boggling.


We went to a spare guestroom and just talked about things and discussed some of the nuances of this venture across the country. Believe it or not, we even pulled out the old microwave popcorn trick as we continued to have a relaxing, intelligent conversation. She even was kind enough to fill me in on all the big words she used. I just sort of scouted out the town the next day, as Annah had to work, and was greatly impressed with the quaint appeal of the little Illinois locale. The similarities to the Groundhog Day movie were eerily familiar, as it’s a small place and I immediately felt like I had been transported inside the actual film. I swear I even saw Punxsutawney Phil himself sheepishly peeking his head out from behind a bush, toying with the thought of seeing his shadow now or waiting until February.


That night we went to a funky, awesome Italian joint to grab some dinner and also talked with some of her friends from town. Later on, Annah showed me around some real estate properties, as she works in that industry in the area. When it came to leaving in the morning, I had kind of a hard time thinking about getting back on the interstate again. It had been restful being off the road for a bit, and I was somewhat daunted at the prospect of the many miles that lay ahead of me.

Plus, I had had a good time with her, at the fantastic hotel, and in the comforts of the town itself. I had even started to feel like I could relate to Murray’s character in the movie somewhat where he relived each day over and over, but in the end, came to appreciate many of the town’s alluring traits.


The city that Oprah built. Or was it Harpo? I said goodbye to Annah, though, and threw a U2 CD in the jukebox as I continued to make my way farther east. Bono was still crooning about something or other as the Sears Tower came into view. Now I have been to Chicago before, but never had the pleasure of seeing this incredible building from a distance through my vehicle’s windshield. The words, “holy crap,” came to mind as the sheer size of the structure dwarfed everything surrounding it. Because it was still a good ways away and seemed a bit hazy, it almost looked like the backdrop of a movie set or something.



As the tower and the other skyscrapers faded in my rearview mirror, I had a renewed energy and was looking forward to my first foray into the great state of Indiana, the childhood home of Mr. David Letterman himself. I was hoping he would be there to greet me at the state line, as I seem to recall him promising his viewers from time to time. The soothing music of the Barenaked Ladies sounded like a good choice as I steadfastly ventured into unknown territory. And no, Mom, they’re not actually naked. In fact, they’re not even ladies … Ciao once more!

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